Glyceryl and glycol acid compounds

ABSTRACT

A composition comprising a glyceryl salicylate compound and/or a glycol salicylate compound. The compositions can be used to reduce the amount of moisture evaporated from skin, protect the skin from UV light, and treat aged or damaged skin.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Application Ser.No. 60/747,760, filed May 19, 2006, the contents of which areincorporated by reference.

BACKGROUND OF THE INVENTION

A. Field of the Invention

The present invention relates generally to a compound that can be usedin compositions such as cosmetic skin care compositions. The compoundcan include an acid molecule attached to a glycerol or glycol moleculevia an ester linkage.

B. Description of Related Art

With ageing, chronic exposure to adverse environmental factors, ormalnutrition, the visual appearance, physical properties, andphysiological functions of skin can change in ways that are consideredvisually undesirable. The most notable and obvious changes include thedevelopment of fine lines and wrinkles, loss of elasticity, increasedsagging, loss of firmness, loss of color evenness or tone, coarsesurface texture, and mottled pigmentation. Less obvious, but measurablechanges which occur as skin ages or endures chronic environmental insultinclude a general reduction in cellular and tissue vitality, reductionin cell replication rates, reduced cutaneous blood flow, reducedmoisture content, accumulated errors in structure and function,alterations in the normal regulation of common biochemical pathways, anda reduction in the skin's ability to remodel and repair itself. Many ofthe alterations in appearance and function of the skin are caused bychanges in the outer epidermal layer of the skin, while others arecaused by changes in the lower dermis.

Several different approaches have been used to treat damaged skin causedby aging, environmental factors, chemicals, or malnutrition. Theseapproaches can oftentimes have various drawbacks, such as significantirritation to the skin or skin toxicity.

SUMMARY OF THE INVENTION

The present invention overcomes deficiencies in the art. In anon-limiting aspect, the invention relates generally to compounds thatcan be used in compositions such as cosmetic and pharmaceuticalcompositions. In certain embodiments, the compound can include an acidmolecule attached to a glyceryl or glycol molecule via an ester linkage.Generic and specific structures of these compounds are disclosedthroughout this specification and incorporated into this section byreference.

In certain embodiments, the compounds can be incorporated into acomposition. The composition can be cosmetic composition or apharmaceutical composition. The composition can be topically applied toskin. The compositions can be included in a cosmetic vehicle.Non-limiting examples of cosmetic vehicles are disclosed in othersections of this specification and are known to those of skill in theart. Examples of cosmetic vehicles include emulsions (e.g., oil-in-waterand water-in-oil emulsions), creams, lotions, solutions (e.g., aqueousor hydro-alcoholic solutions), anhydrous bases (e.g., lipstick or apowder), gels, and ointments. In other non-limiting embodiments, thecompositions of the present invention can be included in anti-aging,cleansing, or moisturizing products. The compositions can also beformulated for topical skin application at least 1, 2, 3, 4, 5, 6, 7, ormore times a day during use. In other aspects of the present invention,compositions can be storage stable or color stable, or both.

In certain embodiments, the compositions of the present invention caninclude from about 0.001% to about 20%, by weight or volume, ofglyceryl/acid or glycol/acid compounds, or a combination of both. Itshould be recognized, however, that the amount of the compounds in acomposition can be modified below, within, or above this range based onthe desired results (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13,14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31,32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49,50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, 99%, or more, byweight or volume of the composition). Therefore, the amount of aglyceryl/acid or glycol/acid compound can include less than 0.001% ormore than 5%, by weight or volume. In other aspects, the compositionscan include 0.002, 0.003, 0.004 . . . 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11,12, 13, 14, 15, 16, 17, 18, 19, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80,90, 95, 96, 97, 98, 99%, or more or, or any range derivable therein, byweight or volume of glyceryl or glycol salicylate or a combination ofboth. In other embodiments, the compositions of the present inventioncan further include a carnitine molecule. The carnitine molecule can beacylated (e.g., acetyl-1-carnitine). In certain aspects, the ratio ofany ingredient within the composition when compared to anotheringredient can be from about 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1,9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1,21:1, 22:1, 23:1, 24:1, 25:1, 26:1, 27:1, 28:1, 29:1, 30:1, 31:1, 32:1,33:1, 34:1, 35:1, 36:1, 37:1, 38:1, 39:1, 40:1, 50:1, 60:1, 70:1, 80:1,90:1, 100:1, or more or any number derivable therein, by weight orvolume of the total composition. In other aspects, the ratio of anyingredient within the composition when compared to another ingredientcan be from about 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11,1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, 1:21, 1:22, 1:23,1:24, 1:25, 1:26, 1:27, 1:28, 1:29, 1:30, 1:31, 1:32, 1:33, 1:34, 1:35,1:36, 1:37, 1:38, 1:39, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90, 1:100, ormore or any number derivable therein, by weight or volume of the totalcomposition.

The compositions of the present invention can also be modified to have adesired oxygen radical absorbance capacity (ORAC) value. In certainnon-limiting aspects, the compositions of the present invention can bemodified to have an ORAC value per mg of at least about 1, 2, 3, 4, 5,6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24,25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 70, 80, 90, 95, 100,200, 300, 400, 500, 600, 700, 800, 900, 1000, 2000, 3000, 4000, 5000,6000, 7000, 8000, 9000, 10000, 15000, 20000, 30000, 50000, 100000 ormore or any range derivable therein.

In other non-limiting aspects of the present invention, the compositionscan further include a vitamin, a mineral, an essential fatty acid, anamino acid (including essential and non-essential amino acids), aflavinoid, and/or a protein, or a combination thereof. Non-limitingexamples of vitamins include the B vitamins (e.g., B1, B2, B6, B12,niacin, folic acid, biotin, and pantothenic acid), vitamin C, vitamin D,vitamin E (e.g., tocopherol or tocopheryl acetate), vitamin A (e.g.,palmitate, retinyl palmitate, or retinoic acid), and vitamin K.Non-limiting examples of minerals include iron, potassium, phosphorus,magnesium, manganese, selenium, and calcium. Non-limiting examples ofessential fatty acids include Omega 3 (linolenic acid), Omega 6(linoleic acid) and Omega 9 (oleic acid) essential fatty acid, or acombination thereof. Non-limiting examples of amino acids includeessential amino acids (e.g., lysine, leucine, isoleucine, methionine,phenylalanine, threonine, tryptophan, valine, histidine, or arginine)and non-essential amino acids (e.g., serine, asparagine, glutamine,aspartic acid, glutamic acid, alanine, tyrosine, cysteine, glycine, orproline). Non-limiting examples of flavinoids include anthocyanincompounds (e.g., cyanidin-3-glucoside and cyanidin-3-rutinoside).

The compositions in non-limiting aspects can have a pH of about 6 toabout 9. In other aspects, the pH can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10,11, 12, 13, or 14. The compositions can include a triglyceride.Non-limiting examples include small, medium, and large chaintriglycerides. In certain aspects, the triglyceride is a medium chaintriglyceride (e.g., caprylic capric triglyceride). The compositions canalso include preservatives. Non-limiting examples of preservativesinclude methylparaben, propylparaben, or a mixture of methylparaben andpropylparaben.

Also disclosed is a method of treating or preventing a skin conditioncomprising topical application of a composition comprising aglyceryl/acid compound and/or a glycol/acid compound, wherein thetopical application of the composition treats the skin condition.Non-limiting examples of skin conditions include pruritus, spider veins,lentigo, age spots, senile purpura, keratosis, melasma, blotches, finelines or wrinkles, nodules, sun damaged skin, dermatitis (including, butnot limited to seborrheic dermatitis, nummular dermatitis, contactdermatitis, atopic dermatitis, exfoliative dermatitis, perioraldermatitis, and stasis dermatitis), psoriasis, folliculitis, rosacea,acne, impetigo, erysipelas, erythrasma, eczema, and other inflammatoryskin conditions. In certain non-limiting aspects, the skin condition canbe caused by exposure to UV light, age, irradiation, chronic sunexposure, environmental pollutants, air pollution, wind, cold, heat,chemicals, disease pathologies, smoking, or lack of nutrition. The skincan be facial skin or non-facial skin (e.g., arms, legs, hands, chest,back, feet, etc.). The method can further comprise identify a person inneed of skin treatment. The person can be a male or female. The age ofthe person can be at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25,30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or more yearsold, or any range derivable therein.

The compositions of the present invention can also be used in methodsfor exfoliate the skin. This allows the user to shed dead skin cells andalso encourages the skin's natural sloughing process. An advantage ofthis process is that it reveals and exposes “younger,” fresher skin. Theshedding process unclogs pores, keeps skin clean and helps reduce acnebreakouts.

The methods of the present invention can also include topically applyingan amount effective to: increase the stratum corneum turnover rate ofthe skin; decrease skin roughness; increase collagen synthesis infibroblasts; increase cellular anti-oxidant defense mechanisms (e.g.,exogenous additions of anti-oxidants can bolster, replenish, or preventthe loss of cellular antioxidants such as catalase and glutathione inskin cells (e.g., keratinocytes, melanocytes, langerhans cells, etc.)which will reduce or prevent oxidative damage to the skin, cellular,proteins, and lipids); inhibit melanin production in melanocytes; reduceor prevent oxidative damage to skin (including reducing the amount lipidperoxides and/or protein oxidation in the skin); enhance desmosomaldegradation, leading to an increase in corneocyte desquamation; increasecytokines, hyaluronic acid, cell proliferation, collagen production andepidermal proliferation; normalize corneocyte cohesion; enhance lipidsynthesis in the intercellular areas; target the sebum in the sebaceousglands; and activate fibroblasts.

The compositions of the present invention can also be used in a regimenalone or with other compositions (e.g., skin care compositions). Forinstance, the composition of the present invention can be applied in themorning and/or evening at predetermined intervals and/or amounts.Alternatively, the compositions of the present invention can be appliedin the morning and a second skin care composition can be applied in theevening and vice versa.

Also disclosed are methods for using the glyceryl/acid compounds andglycol/acid compounds as moisturizing agents, film-forming agents, UVabsorption agents, and/or skin treatment agents. For instance, thecompounds can maintain and/or increase the hydration (such as watercontent) of skin. The compounds can also lubricate the skin. Thecompounds can form a film or barrier on the outer surface of the skinwhich can reduce or prevent the evaporation of water from the skin. Incertain aspects, the film can have tactile properties which make theskin feel soft or smooth. The compounds can also be used as UVabsorption agents and can be used in methods for increasing the UVabsorption characteristics of a composition such as, for example, asunscreen composition. The compounds can be used in methods forincreasing the SPF of a sunscreen composition. In certain aspects, thecompounds can be used to increase the efficiency of existing sunscreenproducts and/or sunscreen agents that are used in such products.Alternatively, the compounds can be used as a stand alone sunscreenagent. In certain embodiments, the compounds can be used in methods forreducing or preventing cosmetic compositions from chemical or physicaldeterioration that is induced by ultraviolet light. The compounds and/orcompositions of the present invention can diffract or absorb a broadspectrum of UV radiation. For example, the compounds and/or compositionscan absorb or diffract UVA (approximately 315 to 400 nm), UVB(approximately 280 to 315) and/or UVC (approximately 10 to 280 nm)light. In certain aspects, the compounds and/or compositions can absorbor diffract UV light ranging from about 1 to about 400 nm, or anyinteger or range therein (e.g., 2, 10, 20, 30, 40, 50, 60, 70, 80, 90,100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230,240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370,380, 390, 399).

Also contemplated are kits that include the compositions of the presentinvention. In certain embodiments, the composition is comprised in acontainer. The container can be a bottle, dispenser, or package. Thecontainer can dispense a pre-determined amount of the composition. Incertain aspects, the compositions is dispensed in a spray or mist,dollop, or liquid. The container can include indicia on its surface. Theindicia can be a word, an abbreviation, a picture, or a symbol.

Also contemplated is a product comprising a composition of the presentinvention. In non-limiting aspects, the product can be a cosmeticproduct. The cosmetic product can be those described in other sectionsof this specification or those known to a person of skill in the art.Non-limiting examples of products include a moisturizer, a cream, alotion, a skin softener, a foundation, a night cream, a lipstick, acleanser, a toner, a sunscreen, a mask, or an anti-aging product.

It is contemplated that any embodiment discussed in this specificationcan be implemented with respect to any method or composition of theinvention, and vice versa. Furthermore, compositions of the inventioncan be used to achieve methods of the invention.

The term “alkyl” includes straight-chain alkyl groups, branched-chainalkyl groups, cycloalkyl (alicyclic) groups, alkylheteroatom-substituted cycloalkyl groups, and cycloalkylheteroatom-substituted alkyl groups.

The term “alkoxy” includes a group having the structure —OR, where R isan alkyl group. Non-limiting examples of alkoxy groups include —OCH₃,—OCH₂CH₃, —OCH₂CH₂CH₃, —OCH(CH₃)₂, —OCH(CH₂)₂, etc.

The term “hydroxyalkyl” includes an alkyl group having at least onehydroxy group.

The term “about” or “approximately” are defined as being close to asunderstood by one of ordinary skill in the art, and in one non-limitingembodiment the terms are defined to be within 10%, within 5%, within 1%,and/or within 0.5%.

The terms “inhibiting” or “reducing” or any variation of these terms,when used in the claims and/or the specification includes any measurabledecrease or complete inhibition to achieve a desired result.

The term “effective,” as that term is used in the specification and/orclaims, means adequate to accomplish a desired, expected, or intendedresult.

The use of the word “a” or “an” when used in conjunction with the term“comprising” in the claims and/or the specification may mean “one,” butit is also consistent with the meaning of “one or more,” “at least one,”and “one or more than one.”

The use of the term “or” in the claims is used to mean “and/or” unlessexplicitly indicated to refer to alternatives only or the alternativesare mutually exclusive, although the disclosure supports a definitionthat refers to only alternatives and “and/or.”

As used in this specification and claim(s), the words “comprising” (andany form of comprising, such as “comprise” and “comprises”), “having”(and any form of having, such as “have” and “has”), “including” (and anyform of including, such as “includes” and “include”) or “containing”(and any form of containing, such as “contains” and “contain”) areinclusive or open-ended and do not exclude additional, unrecitedelements or method steps.

Other objects, features and advantages of the present invention willbecome apparent from the following detailed description. It should beunderstood, however, that the detailed description and the examples,while indicating specific embodiments of the invention, are given by wayof illustration only. Additionally, it is contemplated that changes andmodifications within the spirit and scope of the invention will becomeapparent to those skilled in the art from this detailed description.

DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS

In today's image conscious society, people are continually looking for aproduct that can protect or improve the visual appearance of their skin.Often times, aged skin, uneven skin tone, or skin damaged byenvironmental factors such as UV light, chronic sun exposure,environmental pollutants, chemicals, disease pathologies, or smoking, isassociated with unattractive skin. Compounds of the present inventioncan be used in all types of cosmetic compositions/formulations fortreating, preserving, or preventing the appearance of aged or damagedskin.

For instance, the compounds of the present invention can have a widevariety of uses in compositions that are applied to skin. Non-limitingexamples include using the compounds as a moisturizing agent, afilm-forming agent, a UV absorption agent, and a skin treatment agent.As a moisturizing agent, the compounds can help maintain and/or increasethe hydration of skin, thereby making the skin softer and more pliable.The compounds can also act as lubricants for the skin to treat, reduce,or prevent skin flaking and dry skin.

As a film-forming agent, the compounds can be used to form a film orbarrier on the outer surface of the skin. This can be beneficial to theskin by reducing or preventing the evaporation of water from the skin.Additionally, the film can have tactile properties that make the skinfeel soft and smooth.

As a UV absorption agent, the compounds can be used to protect thecosmetic composition from chemical or physical deterioration induced byultraviolet light. The compounds can also be used as a sunscreen agentin sunscreen compositions. The compounds can also increase the sunprotection factor (SPF) of a sunscreen composition that already includesa sunscreen agent.

As a skin treatment agent, the compounds can be used as activeingredients in topical skin care compositions. Non-limiting examples ofskin conditions that can be treated with the compounds of the presentinvention are disclosed throughout this specification.

These and other aspect of the invention are described in furthernon-limiting detail below.

A. Glyceryl/Acid and Glycol/Acid Compounds

1. Glyceryl/Acid Compounds

A glyceryl/acid compound of the present invention can be derived fromglycerol molecule which has the following structure:

The acid portion of the glyceryl/acid compounds can be attached via anester linkage of the OH group of the glycerol molecule and the COOHgroup of the acid molecule. In non-limiting aspects, a glyceryl/acidcompound can have the following generic chemical structure:

where R, R₁, R₂, R₃, R₄, R₅, and R₆ can each independently be an H, anacid molecule, a hydroxy, a halogen, an oxo (e.g., ether), an alkoxy, asilyloxy, an acyl, an aryl, an acetyl, a carbonyl, a cyano, aheterocyclyl, an amido, an aminocarbonyl, an amino, —NH-alkyl,—N(alkyl)₂, —NH-(substituted alkyl), —N-(substituted alkyl)₂, —NH-aryl,—N(aryl)₂, an azido, a trialkylsilyloxy, an acyloxy, a acylamino, abis-acylamino, an ester, a NO, a NO₂, or a sulfo (e.g., thioether,thioester, thiocarbonyl, sulfonamido, sulfonyl, etc.). In certainaspects, the acid molecule is selected from the group consisting ofsalicylic acid, cinnamic acid, and benzoic acid, and derivatives andsubstituted acids thereof. Other non-limiting examples of acids that canbe used in the context of the present invention are described inInternational Cosmetic Ingredient Dictionary and Handbook, 10^(th) Ed.,2004, which is incorporated by reference. In certain aspects, at leastone of R, R₄, and R₆ is an acid, R and R₄ are acids, R and R₆ are acids,R₄ and R₆ are acids, or R, R₄, and R₆ are all acids. Non-limitingexamples of certain glyceryl/acid compounds of the present invention areillustrated below:

The glyceryl/acid compounds and derivatives and modifications of thesame can be prepared by using convention chemical synthesis techniques(see, e.g., Organic Chemistry, 5^(th) Ed.).

2. Glycol/Acid Compounds

A glycol/acid compound of the present invention can be derived from aglycol molecule. Glycols are a generic class of dihydric alcohols.Non-limiting examples of glycols that can be used in the context of thepresent invention include: ethylene glycols (e.g., 1, 2 ethane diol(monoethylene glycol), 2-hydroxyethoxy)ethan-2-ol (diethylene glycol);polyethylene glycols (PEGs); propylene glycols (e.g., 1,2 propane diol,1,3 propane diol, etc.); and butylene glycols (e.g., 1,2 butane diol,1,3 butane diol, 1,4 butane diol, etc.). Other non-limiting examples ofglycols that can be used in the context of the present invention aredescribed in International Cosmetic Ingredient Dictionary and Handbook,10^(th) Ed., 2004, which is incorporated by reference. It certainaspects, the glycol that is used can have similar physical and chemicalcharacteristics to glycerol.

The acid portion of the glycol/acid compounds can be attached via anester linkage of the OH group of the glycol molecule and the COOH groupof the acid molecule. In non-limiting aspects, a glycol/acid compoundcan have the following generic chemical structure:

where n can be 2, 3, 4, 5, 6, 7, 8, 9, 10, or more, or any rangetherein. In certain aspects, n is an integer from 2 to 4. Y₁, Y₂, Y₃,and Y₄, can each independently be OY₅, an H, an acid molecule attachedvia an ester linkage, a hydroxy, a halogen, an oxo (e.g., ether), analkoxy, a silyloxy, an acyl, an aryl, an acetyl, a carbonyl, a cyano, aheterocyclyl, an amido, an aminocarbonyl, an amino, —NH-alkyl,—N(alkyl)₂, —NH-(substituted alkyl), —N-(substituted alkyl)₂, —NH-aryl,—N(aryl)₂, an azido, a trialkylsilyloxy, an acyloxy, a acylamino, abis-acylamino, an ester, a NO, a NO₂, or a sulfo (e.g., thioether,thioester, thiocarbonyl, sulfonamido, sulfonyl, etc.). In certainaspects, the acid molecule is selected from the group consisting ofsalicylic acid, cinnamic acid, and benzoic acid, and derivatives andsubstituted acids thereof. Other non-limiting examples of acids that canbe used in the context of the present invention are described inInternational Cosmetic Ingredient Dictionary and Handbook, 10^(th) Ed.,2004, which is incorporated by reference. Y₅ can be anyone of the groupsidentified for Y₁, Y₂, Y₃, and Y₄. In certain aspects Y₅ is an acidgroup. In other embodiments, at least two of Y₁, Y₂, Y₃, and Y₄ is ahydroxyl group. Non-limiting examples of certain particular glycol/acidcompounds of the present invention are illustrated below:

The glycol/acid compounds and derivatives and modifications of the samecan be prepared by using convention chemical synthesis techniques (see,e.g., Organic Chemistry, 5^(th) Ed.).

3. Modifications and Derivatives of Glyceryl/Glycol/Acid Compounds

Modifications or derivatives of the glyceryl/acid and glycol/acidcompounds disclosed throughout this specification are contemplated asbeing useful with the methods and compositions of the present invention.Derivatives and modifications may be prepared and the properties of suchderivatives and modified compounds may be assayed for their desiredproperties by any method known to those of skill in the art.

In certain aspects, “derivative” refers to a chemically modifiedglyceryl/acid or glycol/acid compound that still retains the desiredeffects of the compound prior to the chemical modification. Suchderivatives may have the addition, removal, or substitution of one ormore chemical moieties on the glyceryl, glycol, and/or acid portion ofthe compounds. Non-limiting examples of the modifications that can bemade to these portions of the compounds include the addition or removalof alkyl groups, carboxyl groups, carbonyl groups, hydroxyl groups,nitro groups, amino groups, amide groups, azo groups, sulfate groups,sulfonate groups, sulfono groups, sulfhydryl groups, sulfonyl groups,sulfoxido groups, phosphate groups, phosphono groups, phosphoryl groups,and/or halide groups. Additional modifications can include an additionor a deletion of one or more atoms of the atomic framework, for example,substitution of an ethyl by a propyl or substitution of a phenyl by alarger or smaller aromatic group. In a cyclic or bicyclic structure,hetero atoms such as N, S, or O can be substituted into the structureinstead of a carbon atom.

B Compositions

The compounds of the present invention can be incorporated into alltypes of compositions (e.g., cosmetic and pharmaceutical compositions).A person of ordinary skill would recognize that the compositions caninclude any number of combinations of glyceryl/acid compounds,glycol/acid compounds, and/or additional ingredients, or derivativesthereof. The concentrations of the glyceryl/acid compounds, glycol/acidcompounds, and/or additional ingredients, or derivatives thereof, canvary for a given composition. This variation can oftentimes depend onthe desired characteristics of the final composition. In non-limitingembodiments, for example, the compositions may include in their finalform, for example, at least about 0.0001%, 0.0002%, 0.0003%, 0.0004%,0.0005%, 0.0006%, 0.0007%, 0.0008%, 0.0009%, 0.0010%, 0.0011%, 0.0012%,0.0013%, 0.0014%, 0.0015%, 0.0016%, 0.0017%, 0.0018%, 0.0019%, 0.0020%,0.0021%, 0.0022%, 0.0023%, 0.0024%, 0.0025%, 0.0026%, 0.0027%, 0.0028%,0.0029%, 0.0030%, 0.0031%, 0.0032%, 0.0033%, 0.0034%, 0.0035%, 0.0036%,0.0037%, 0.0038%, 0.0039%, 0.0040%, 0.0041%, 0.0042%, 0.0043%, 0.0044%,0.0045%, 0.0046%, 0.0047%, 0.0048%, 0.0049%, 0.0050%, 0.0051%, 0.0052%,0.0053%, 0.0054%, 0.0055%, 0.0056%, 0.0057%, 0.0058%, 0.0059%, 0.0060%,0.0061%, 0.0062%, 0.0063%, 0.0064%, 0.0065%, 0.0066%, 0.0067%, 0.0068%,0.0069%, 0.0070%, 0.0071%, 0.0072%, 0.0073%, 0.0074%, 0.0075%, 0.0076%,0.0077%, 0.0078%, 0.0079%, 0.0080%, 0.0081%, 0.0082%, 0.0083%, 0.0084%,0.0085%, 0.0086%, 0.0087%, 0.0088%, 0.0089%, 0.0090%, 0.0091%, 0.0092%,0.0093%, 0.0094%, 0.0095%, 0.0096%, 0.0097%, 0.0098%, 0.0099%, 0.0100%,0.0200%, 0.0250%, 0.0275%, 0.0300%, 0.0325%, 0.0350%, 0.0375%, 0.0400%,0.0425%, 0.0450%, 0.0475%, 0.0500%, 0.0525%, 0.0550%, 0.0575%, 0.0600%,0.0625%, 0.0650%, 0.0675%, 0.0700%, 0.0725%, 0.0750%, 0.0775%, 0.0800%,0.0825%, 0.0850%, 0.0875%, 0.0900%, 0.0925%, 0.0950%, 0.0975%, 0.1000%,0.1250%, 0.1500%, 0.1750%, 0.2000%, 0.2250%, 0.2500%, 0.2750%, 0.3000%,0.3250%, 0.3500%, 0.3750%, 0.4000%, 0.4250%, 0.4500%, 0.4750%, 0.5000%,0.5250%, 0.0550%, 0.5750%, 0.6000%, 0.6250%, 0.6500%, 0.6750%, 0.7000%,0.7250%, 0.7500%, 0.7750%, 0.8000%, 0.8250%, 0.8500%, 0.8750%, 0.9000%,0.9250%, 0.9500%, 0.9750%, 1.0%, 1.1%, 1.2%, 1.3%, 1.4%, 1.5%, 1.6%,1.7%, 1.8%, 1.9%, 2.0%, 2.1%, 2.2%, 2.3%, 2.4%, 2.5%, 2.6%, 2.7%, 2.8%,2.9%, 3.0%, 3.1%, 3.2%, 3.3%, 3.4%, 3.5%, 3.6%, 3.7%, 3.8%, 3.9%, 4.0%,4.1%, 4.2%, 4.3%, 4.4%, 4.5%, 4.6%, 4.7%, 4.8%, 4.9%, 5.0%, 5.1%, 5.2%,5.3%, 5.4%, 5.5%, 5.6%, 5.7%, 5.8%, 5.9%, 6.0%, 6.1%, 6.2%, 6.3%, 6.4%,6.5%, 6.6%, 6.7%, 6.8%, 6.9%, 7.0%, 7.1%, 7.2%, 7.3%, 7.4%, 7.5%, 7.6%,7.7%, 7.8%, 7.9%, 8.0%, 8.1%, 8.2%, 8.3%, 8.4%, 8.5%, 8.6%, 8.7%, 8.8%,8.9%, 9.0%, 9.1%, 9.2%, 9.3%, 9.4%, 9.5%, 9.6%, 9.7%, 9.8%, 9.9%, 10%,11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%,25%, 26%, 27%, 28%, 29%, 30%, 35%, 40%, 45%, 50%, 60%, 65%, 70%, 75%,80%, 85%, 90%, 95%, or 99% or any range derivable therein, of at leastone of the glyceryl/acid compounds, glycol/acid compounds, and/oradditional ingredients, or derivatives thereof. In certain non-limitingaspects, the percentages can be calculated by weight or volume of thetotal composition. A person of ordinary skill in the art wouldunderstand that the concentrations can vary depending on the addition,substitution, and/or subtraction of the glyceryl/acid compounds,glycol/acid compounds, and additional ingredients, or derivativesthereof.

C Additional Ingredients

In addition to the glyceryl/acid compounds and/or glycol/acid compoundsdisclosed throughout this specification, compositions of the presentinvention can include additional ingredients such as cosmeticingredients and pharmaceutical active ingredients. Non-limiting examplesof these additional ingredients are described in the followingsubsections.

1. Cosmetic Ingredients

The CTFA International Cosmetic Ingredient Dictionary and Handbook(2004) describes a wide variety of non-limiting cosmetic ingredientsthat can be used in the context of the present invention. Examples ofthese ingredient classes include: fragrances (artificial and natural),dyes and color ingredients (e.g., Blue 1, Blue 1 Lake, Red 40, titaniumdioxide, D&C blue no. 4, D&C green no. 5, D&C orange no. 4, D&C red no.17, D&C red no. 33, D&C violet no. 2, D&C yellow no. 10, and D&C yellowno. 11), adsorbents, lubricants, solvents, moisturizers (including,e.g., emollients, humectants, film formers, occlusive agents, and agentsthat affect the natural moisturization mechanisms of the skin),water-repellants, UV absorbers (physical and chemical absorbers such asparaaminobenzoic acid (“PABA”) and corresponding PABA derivatives,titanium dioxide, zinc oxide, etc.), essential oils, vitamins (e.g. A,B, C, D, E, and K), trace metals (e.g. zinc, calcium and selenium),anti-irritants (e.g. steroids and non-steroidal anti-inflammatories),botanical extracts (e.g. aloe vera, chamomile, cucumber extract, ginkgobiloba, ginseng, and rosemary), anti-microbial agents, antioxidants(e.g., BHT and tocopherol), chelating agents (e.g., disodium EDTA andtetrasodium EDTA), preservatives (e.g., methylparaben andpropylparaben), pH adjusters (e.g., sodium hydroxide and citric acid),absorbents (e.g., aluminum starch octenylsuccinate, kaolin, corn starch,oat starch, cyclodextrin, talc, and zeolite), skin bleaching andlightening agents (e.g., hydroquinone and niacinamide lactate),humectants (e.g., sorbitol, urea, and manitol), exfoliants,waterproofing agents (e.g., magnesium/aluminum hydroxide stearate), skinconditioning agents (e.g., aloe extracts, allantoin, bisabolol,ceramides, dimethicone, hyaluronic acid, and dipotassium glycyrrhizate).Non-limiting examples of some of these ingredients are provided in thefollowing subsections.

a. Preservatives

Non-limiting examples of preservatives that can be used in the contextof the present invention include quaternary ammonium preservatives suchas polyquarternium-1 and benzalkonium halides (e.g., benzalkoniumchloride (“BAC”) and benzalkonium bromide), parabens (e.g.,methylparabens and propylparabens), phenoxyethanol, benzyl alcohol,chlorobutanol, phenol, sorbic acid, thimerosal or combinations thereof.

b. Moisturizers

Non-limiting examples of moisturizing agents that can be used with thecompositions of the present invention can be found in the InternationalCosmetic Ingredient Dictionary, 10^(th) Ed., 2004. Examples includeamino acids, chondroitin sulfate, diglycerin, erythritol, fructose,glucose, 1,2,6-hexanetriol, honey, hyaluronic acid, hydrogenated honey,hydrogenated starch hydrolysate, inositol, lactitol, maltitol, maltose,mannitol, natural moisturizing factor, salts of pyrollidone carboxylicacid, potassium PCA, sodium glucuronate, sodium PCA, sorbitol, sucrose,trehalose, urea, and xylitol.

c. Emollients

Non-limiting examples of emollients include, but are not limited to,vegetable oils, mineral oils, silicone oils, synthetic and naturalwaxes, petrolatum, lanolin, aluminum magnesium hydroxide stearate (whichcan also function as a water repellent), and fatty acid esters.Non-limiting examples of vegetable oils include safflower oil, corn oil,sunflower seed oil, and olive oil.

d. Antioxidants

Non-limiting examples of antioxidants include, but are not limited to,acetyl cysteine, ascorbic acid, ascorbic acid polypeptide, ascorbyldipalmitate, ascorbyl methylsilanol pectinate, ascorbyl palmitate,ascorbyl stearate, BHA, BHT, t-butyl hydroquinone, cysteine, cysteineHCl, diamylhydroquinone, di-t-butylhydroquinone, dicetylthiodipropionate, dioleyl tocopheryl methylsilanol, disodium ascorbylsulfate, distearyl thiodipropionate, ditridecyl thiodipropionate,dodecyl gallate, erythorbic acid, esters of ascorbic acid, ethylferulate, ferulic acid, gallic acid esters, hydroquinone, isooctylthioglycolate, kojic acid, magnesium ascorbate, magnesium ascorbylphosphate, methylsilanol ascorbate, natural botanical anti-oxidants suchas green tea or grape seed extracts, nordihydroguaiaretic acid, octylgallate, phenylthioglycolic acid, potassium ascorbyl tocopherylphosphate, potassium sulfite, propyl gallate, quinones, rosmarinic acid,sodium ascorbate, sodium bisulfite, sodium erythorbate, sodiummetabisulfite, sodium sulfite, superoxide dismutase, sodiumthioglycolate, sorbityl furfural, thiodiglycol, thiodiglycolamide,thiodiglycolic acid, thioglycolic acid, thiolactic acid, thiosalicylicacid, tocophereth-5, tocophereth-10, tocophereth-12, tocophereth-18,tocophereth-50, tocopherol, tocophersolan, tocopheryl acetate,tocopheryl linoleate, tocopheryl nicotinate, tocopheryl succinate, andtris(nonylphenyl)phosphite.

e. Thickening Agents

Thickening agents, including thickener or gelling agents, includesubstances which that can increase the viscosity of a composition.Thickeners include those that can increase the viscosity of acomposition without substantially modifying the efficacy of theingredients within the composition. Thickeners can also increase thestability of the compositions of the present invention. Non-limitingexamples of additional thickeners that are known to those of ordinaryskill in the art can be used in the context of the present invention(e.g., U.S. Pat. Nos. 5,087,445; 4,509,949; 2,798,053; InternationalCosmetic Ingredient Dictionary and Handbook, 10^(th) Ed., 2004).Examples include carboxylic acid polymers, crosslinked polyacrylatepolymers, polyacrylamide polymers, polysaccharides, and gums. Examplesof carboxylic acid polymers include crosslinked compounds containing oneor more monomers derived from acrylic acid, substituted acrylic acids,and salts and esters of these acrylic acids and the substituted acrylicacids, wherein the crosslinking agent contains two or more carbon-carbondouble bonds and is derived from a polyhydric alcohol. Examples ofcommercially available carboxylic acid polymers include carbomers, whichare homopolymers of acrylic acid crosslinked with allyl ethers ofsucrose or pentaerytritol (e.g., Carbopol™ 900 series from B.F.Goodrich).

f. Silicone Containing Compounds

In non-limiting aspects, silicone containing compounds include anymember of a family of polymeric products whose molecular backbone ismade up of alternating silicon and oxygen atoms with side groupsattached to the silicon atoms. By varying the —Si—O— chain lengths, sidegroups, and crosslinking, silicones can be synthesized into a widevariety of materials. They can vary in consistency from liquid to gel tosolids.

The silicone containing compounds that can be used in the context of thepresent invention include those described in this specification or thoseknown to a person of ordinary skill in the art. Non-limiting examplesinclude silicone oils (e.g., volatile and non-volatile oils), gels, andsolids. The silicon containing compound can be a silicone oil such as apolyorganosiloxane. Non-limiting examples of polyorganosiloxanes includedimethicone, cyclomethicone, polysilicone-11, phenyl trimethicone,trimethylsilylamodimethicone, stearoxytrimethylsilane, or mixtures ofthese and other organosiloxane materials in any given ratio in order toachieve the desired consistency and application characteristicsdepending upon the intended application (e.g., to a particular area suchas the skin, hair, or eyes). A “volatile silicone oil” includes asilicone oil have a low heat of vaporization, i.e. normally less thanabout 50 cal per gram of silicone oil. Non-limiting examples of volatilesilicone oils include: cyclomethicones such as Dow Corning 344 Fluid,Dow Corning 345 Fluid, Dow Corning 244 Fluid, and Dow Corning 245 Fluid,Volatile Silicon 7207 (Union Carbide Corp., Danbury, Conn.); lowviscosity dimethicones, i.e. dimethicones having a viscosity of about 50cst or less (e.g., dimethicones such as Dow Corning 200-0.5 cst Fluid).The Dow Corning Fluids are available from Dow Corning Corporation,Midland, Mich. Cyclomethicone and dimethicone are described inInternational Cosmetic Ingredient Dictionary, 10^(th) Ed., 2004 ascyclic dimethyl polysiloxane compounds and a mixture of fully methylatedlinear siloxane polymers end-blocked with trimethylsiloxy units,respectively. Other non-limiting volatile silicone oils that can be usedin the context of the present invention include those available fromGeneral Electric Co., Silicone Products Div., Waterford, N.Y. and SWSSilicones Div. of Stauffer Chemical Co., Adrian, Mich.

2. Pharmaceutical Actives

Pharmaceutical active agents are also contemplated as being useful withthe compositions of the present invention. Non-limiting examples ofpharmaceutical active agents include anti-acne agents, agents used totreat rosacea, analgesics, anesthetics, anorectals, antihistamines,anti-inflammatory agents including non-steroidal anti-inflammatorydrugs, antibiotics, antifungals, antivirals, antimicrobials, anti-canceractives, scabicides, pediculicides, antineoplastics, antiperspirants,antipruritics, antipsoriatic agents, antiseborrheic agents, biologicallyactive proteins and peptides, burn treatment agents, cauterizing agents,depigmenting agents, depilatories, diaper rash treatment agents,enzymes, hair growth stimulants, hair growth retardants including DFMOand its salts and analogs, hemostatics, kerotolytics, canker soretreatment agents, cold sore treatment agents, dental and periodontaltreatment agents, photosensitizing actives, skin protectant/barrieragents, steroids including hormones and corticosteroids, sunburntreatment agents, sunscreens, transdermal actives, nasal actives,vaginal actives, wart treatment agents, wound treatment agents, woundhealing agents, etc.

D Vehicles

Compositions of the present invention can be incorporated into all typesof vehicles. Non-limiting examples of suitable vehicles includeemulsions (e.g., water-in-oil, water-in-oil-in-water, oil-in-water,oil-in-water-in-oil, oil-in-water-in-silicone, water-in-silicone,silicone-in-water emulsions), creams, lotions, solutions (both aqueousand hydro-alcoholic), anhydrous bases (such as lipsticks and powders),gels, and ointments or by other method or any combination of theforgoing as would be known to one of ordinary skill in the art (see,e.g., Remington's, 1990 and International Cosmetic Ingredient Dictionaryand Handbook, 10^(th) Ed., 2004)). Variations and other appropriatevehicles will be apparent to the skilled artisan and are appropriate foruse in the present invention. In certain aspects, it is important thatthe concentrations and combinations of the compounds, ingredients, andagents be selected in such a way that the combinations are chemicallycompatible and do not form complexes which precipitate from the finishedproduct.

E Cosmetic Products and Articles of Manufacture

The composition of the present invention can also be used in manycosmetic products including, but not limited to, sunscreen products,sunless skin tanning products, hair products, finger nail products,moisturizing creams, skin benefit creams and lotions, softeners, daylotions, gels, ointments, foundations, night creams, lipsticks,cleansers, toners, masks, or other known cosmetic products orapplications. Additionally, the cosmetic products can be formulated asleave-on or rinse-off products. In certain aspects, the compositions ofthe present invention are stand-alone products.

F Kits

Kits are also contemplated as being used in certain aspects of thepresent invention. For instance, emulsion compositions of the presentinvention can be included in a kit. A kit can include a container.Containers can include a bottle, a metal tube, a laminate tube, aplastic tube, a dispenser, a pressurized container, a barrier container,a package, a compartment, a lipstick container, a compact container,cosmetic pans that can hold cosmetic compositions, or other types ofcontainers such as injection or blow-molded plastic containers intowhich the dispersions or compositions or desired bottles, dispensers, orpackages are retained. The kit and/or container can include indicia onits surface. The indicia, for example, can be a word, a phrase, anabbreviation, a picture, or a symbol.

The containers can dispense a pre-determined amount of the emulsioncomposition. In other embodiments, the container can be squeezed (e.g.,metal, laminate, or plastic tube) to dispense a desired amount of theemulsion composition. The emulsion composition can be dispensed as aspray, an aerosol, a liquid, a fluid, or a semi-solid. The containerscan have spray, pump, or squeeze mechanisms. A kit can also includeinstructions for employing the kit components as well the use of anyother emulsion compositions included in the container. Instructions caninclude an explanation of how to apply, use, and maintain the emulsioncompositions.

EXAMPLES

The following examples are included to demonstrate certain non-limitingaspects of the invention. It should be appreciated by those of skill inthe art that the techniques disclosed in the examples which followrepresentative techniques discovered by the inventor to function well inthe practice of the invention. However, those of skill in the art shouldappreciate that changes can be made in the specific embodiments whichare disclosed and still obtain a like or similar result withoutdeparting from the spirit and scope of the invention.

Example 1 Methods of Making Glyceryl/Acid or Glycol Acid Compounds

An esterification process can be used for producing glyceryl/acid andglycol/acid compounds. A glyceryl or glycol molecule and an acidmolecule are added to a multi-necked round bottom flask equipped with aheating mantle, a condenser, a Dean-Stark trap and a thermometer. Asolvent is chosen that will allow a high enough reflux temperature toaccommodate the reaction. The reaction is run until the calculatedamount of water is collected in the trap signifying that the limitingreagent is exhausted. The by-product can be compounds other than waterin some processes. For instance, if a methyl salicylate is used in placeof salicylic acid, methanol will be the by-product rather than water,and the methanol may escape through the condenser or remain in thereaction flask. The methanol can be removed when the ester is extracted.

Example 2 UV Absorption Data for Glyceryl Mono-Salicylate

UV absorption data for glyceryl mono-salicylate is summarized in Table 1below:

TABLE 1 (UV absorption data*) Glyceryl Mono-Salicylate Data Avg. Mol.Wt. 242.95 Molar Absorptivity (λ max 238 nm) 12065.7 Molar Absorptivity(λ max 307 nm) 6126.4 *Data obtained by using a UV/Vis spectrometerusing standard USP 197U testing procedures.

Example 3 Compositions

Non-limiting examples of compositions of the present invention aredescribed in Tables 1-3.

TABLE 2* (Exfoliation composition) Ingredient % Concentration (byweight) SD Alcohol 40-B 56.00 Glyceryl mono-salicylate** 7.50 Water29.00 Mineral oil 3.00 Sepigel 305 (thickener) 4.00 *The composition wasprepared as follows: Ingredients were cold-mixed and added to a beakerin the listed order prior to the addition of the next ingredient. The pHof the composition was adjusted to approximately 4.3 by using 1N HClsolution. **Glyceryl mono-salicylate can be substituted with otherglyceryl/acid and glycol/acid compounds.

TABLE 3* (Moisturizer**) Ingredient % Concentration (by weight) Phase AWater 66.44 Xanthum gum 0.10 Methyl paraben 0.15 Propyl paraben 0.10Citric acid 0.01 Phase B Cetyl alcohol 4.00 Glyceryl stearate + PEG 1004.00 Octyl palmitate 4.00 Dimethicone 1.00 Tocopheryl acetate 0.20 PhaseC SD Alcohol 40-B 15.00 Glyceryl mono-salicylate*** 5.00 *Thecomposition was prepared as follows: Phases A and B were heated toapproximately 70° C.-75° C. in separate beakers while mixing. Phase Bwas added to Phase A when both phases were at approximately 70° C.-75°C. The Phase A + B mixture was cooled to <40° C. while mixing. Phase Cwas subsequently added to the Phase A + B mixture, and the mixture wascooled to room temperature (approximately 20° C.-25° C.) while mixing.**Formulation showed statistically significant moisturization for 6hours after application to skin when compared to the baseline control (p< 0.05) (data not shown). ***Glyceryl mono-salicylate can be substitutedwith other glyceryl/acid and glycol/acid compounds.

TABLE 4 (Generic formulation)* Ingredient % Concentration (by weight)Phase A Water 84.44 Xanthum gum 0.1 M-paraben 0.15 P-paraben 0.1 Citricacid 0.01 Phase B Cetyl alcohol 4.0 Glyceryl stearate + PEG 100 4.0Octyl palmitate 4.0 Dimethicone 1.0 Tocopheryl acetate 0.2 Phase CGlyceryl mono-salicylate** 2.0 *The composition can be prepared asfollows: Sprinkle Xanthum gum in water and mix for 10 min. Subsequently,add all ingredients in phase A and heat to 70-75° C. Add all items inphase B to a separate beaker and heat to 70-75° C. Mix phases A and B at70-75° C. Continue mixing and allow composition to cool to 30° C.Subsequently, add phase C ingredient while mixing. **Glycerylmono-salicylate can be substituted with other glyceryl/acid andglycol/acid compounds.

TABLE 5 (Generic formulation)* Ingredient % Concentration (by weight)Phase A Water 78.6 M-paraben 0.2 P-paraben 0.1 Na2 EDTA 0.1 Shea butter4.5 Petrolatum 4.5 Glycerin 4.0 Propylene Glycol 2.0 Finsolve TN 2.0Phase B Sepigel 305 2.0 Phase C Glyceryl mono-salicylate** 2.0 *Addingredients in phase A to beaker and heat to 70-75° C. while mixing.Subsequently, add the phase B ingredient with phase A and cool to 30° C.with mixing. Subsequently, add phase C ingredient while mixing.**Glyceryl mono-salicylate can be substituted with other glyceryl/acidand glycol/acid compounds.

TABLE 6 (Generic formulation)* Ingredient % Concentration (by weight)Phase A Water 84.44 Xanthum gum 0.1 M-paraben 0.15 P-paraben 0.1 Citricacid 0.01 Phase B Cetyl alcohol 4.0 Glyceryl stearate + PEG 100 4.0Octyl palmitate 4.0 Dimethicone 1.0 Tocopheryl acetate 0.2 Phase CGlyceryl mono-salicylate** 1.0 Glycol mono-salicylate** 1.0 *Thecomposition can be prepared as follows: Sprinkle Xanthum gum in waterand mix for 10 min. Subsequently, add all ingredients in phase A andheat to 70-75° C. Add all items in phase B to separate beaker and heatto 70-75° C. Mix phases A and B at 70-75° C. Continue mixing and allowcomposition to cool to 30° C. Subsequently, add phase C ingredient whilemixing. **Glyceryl mono-salicylate and/or glycol mono-salicylate can besubstituted with other glyceryl/acid and glycol/acid compounds.

TABLE 7 (Generic formulation)* Ingredient % Concentration (by weight)Phase A Water 78.6 M-paraben 0.2 P-paraben 0.1 Na2 EDTA 0.1 Shea butter4.5 Petrolatum 4.5 Glycerin 4.0 Propylene Glycol 2.0 Finsolve TN 2.0Phase B Sepigel 305 2.0 Phase C Glyceryl mono-salicylate** 1.0 Glycolmono-salicylate** 1.0 *Add ingredients in phase A to beaker and heat to70-75° C. while mixing. Subsequently, add the phase B ingredient withphase A and cool to 30° C. with mixing. Subsequently, add phase Cingredient while mixing. **Glyceryl mono-salicylate and/or glycolmono-salicylate can be substituted with other glyceryl/acid andglycol/acid compounds.

Example 4 Determining Efficacy of Glyceryl/Acid or Glycol/Acid Compoundsand Compositions

The efficacy of the glyceryl/acid or glycol/acid compounds andcompositions containing the same can be determined by methods known tothose of ordinary skill in the art. The following are non-limitingprocedures that can be used in the context of the present invention. Itshould be recognized that other testing procedures can be used,including, for example, objective and subjective procedures.

Skin moisture/hydration can be measured by using impedance measurementswith the Nova Dermal Phase Meter. The impedance meter measures changesin skin moisture content. The outer layer of the skin has distinctelectrical properties. When skin is dry it conducts electricity verypoorly. As it becomes more hydrated increasing conductivity results.Consequently, changes in skin impedance (related to conductivity) can beused to assess changes in skin hydration. The unit can be calibratedaccording to instrument instructions for each testing day. A notation oftemperature and relative humidity can also be made. Subjects can beevaluated as follows: prior to measurement they can equilibrate in aroom with defined humidity (e.g., 30-50%) and temperature (e.g., 68-72C). Three separate impedance readings can be taken on each side of theface, recorded, and averaged. The T5 setting can be used on theimpedance meter which averages the impedance values of every fiveseconds application to the face. Changes can be reported withstatistical variance and significance.

Skin clarity and the reduction in freckles and age spots can beevaluated using a Minolta Chromometer. Changes in skin color can beassessed to determine irritation potential due to product treatmentusing the a* values of the Minolta Chroma Meter. The a* value measureschanges in skin color in the red region. This is used to determinewhether a composition is inducing irritation. The measurements can bemade on each side of the face and averaged, as left and right facialvalues. Skin clarity can also be measured using the Minolta Meter. Themeasurement is a combination of the a*, b, and L values of the MinoltaMeter and is related to skin brightness, and correlates well with skinsmoothness and hydration. Skin reading is taken as above. In onenon-limiting aspect, skin clarity can be described as L/C where C ischroma and is defined as (a²+b²)^(1/2).

Skin dryness, surface fine lines, skin smoothness, and skin tone can beevaluated with clinical grading techniques. For example, clinicalgrading of skin dryness can be determined by a five point standardKligman Scale: (0) skin is soft and moist; (1) skin appears normal withno visible dryness; (2) skin feels slightly dry to the touch with novisible flaking; (3) skin feels dry, tough, and has a whitish appearancewith some scaling; and (4) skin feels very dry, rough, and has a whitishappearance with scaling. Evaluations can be made independently by twoclinicians and averaged.

Clinical grading of skin tone can be performed via a ten point analognumerical scale: (10) even skin of uniform, pinkish brown color. Nodark, erythremic, or scaly patches upon examination with a hand heldmagnifying lens. Microtexture of the skin very uniform upon touch; (7)even skin tone observed without magnification. No scaly areas, butslight discolorations either due to pigmentation or erythema. Nodiscolorations more than 1 cm in diameter; (4) both skin discolorationand uneven texture easily noticeable. Slight scaliness. Skin rough tothe touch in some areas; and (1) uneven skin coloration and texture.Numerous areas of scaliness and discoloration, either hypopigmented,erythremic or dark spots. Large areas of uneven color more than 1 cm indiameter. Evaluations were made independently by two clinicians andaveraged.

Clinical grading of skin smoothness can be analyzed via a ten pointanalog numerical scale: (10) smooth, skin is moist and glistening, noresistance upon dragging finger across surface; (7) somewhat smooth,slight resistance; (4) rough, visibly altered, friction upon rubbing;and (1) rough, flaky, uneven surface. Evaluations were madeindependently by two clinicians and averaged.

Skin smoothness and wrinkle reduction can also be assessed visually byusing the methods disclosed in Packman and Gams (1978). For example, ateach subject visit, the depth, shallowness and the total number ofsuperficial facial lines (SFLs) of each subject can be carefully scoredand recorded. A numerical score was obtained by multiplying a numberfactor times a depth/width/length factor. Scores are obtained for theeye area and mouth area (left and right sides) and added together as thetotal wrinkle score.

Skin firmness can be measured using a Hargens ballistometer, a devicethat evaluates the elasticity and firmness of the skin by dropping asmall body onto the skin and recording its first two rebound peaks. Theballistometry is a small lightweight probe with a relatively blunt tip(4 square mm-contact area) was used. The probe penetrates slightly intothe skin and results in measurements that are dependent upon theproperties of the outer layers of the skin, including the stratumcorneum and outer epidermis and some of the dermal layers.

Skin softness/suppleness can be evaluated using the Gas BearingElectrodynamometer, an instrument that measures the stress/strainproperties of the skin. The viscoelastic properties of skin correlatewith skin moisturization. Measurements can be obtained on thepredetermined site on the cheek area by attaching the probe to the skinsurface with double-stick tape. A force of approximately 3.5 gm can beapplied parallel to the skin surface and the skin displacement isaccurately measured. Skin suppleness can then be calculated and isexpressed as DSR (Dynamic Spring Rate in gm/mm).

The appearance of lines and wrinkles on the skin can be evaluated usingreplicas, which is the impression of the skin's surface. Silicone rubberlike material can be used. The replica can be analyzed by imageanalysis. Changes in the visibility of lines and wrinkles can beobjectively quantified via the taking of silicon replicas form thesubjects' face and analyzing the replicas image using a computer imageanalysis system. Replicas can be taken from the eye area and the neckarea, and photographed with a digital camera using a low angle incidencelighting. The digital images can be analyzed with an image processingprogram and the are of the replicas covered by wrinkles or fine lineswas determined.

The surface contour of the skin can be measured by using theprofilometer/Stylus method. This includes either shining a light ordragging a stylus across the replica surface. The vertical displacementof the stylus can be fed into a computer via a distance transducer, andafter scanning a fixed length of replica a cross-sectional analysis ofskin profile can be generated as a two-dimensional curve. This scan canbe repeated any number of times along a fix axis to generate a simulated3-D picture of the skin. Ten random sections of the replicas using thestylus technique can be obtained and combined to generate averagevalues. The values of interest include Ra which is the arithmetic meanof all roughness (height) values computed by integrating the profileheight relative to the mean profile height. Rt which is the maximumvertical distance between the highest peak and lowest trough, and Rzwhich is the mean peak amplitude minus the mean peak height. Values aregiven as a calibrated value in mm. Equipment should be standardizedprior to each use by scanning metal standards of know values. Ra Valuecan be computed by the following equation: R_(a)=Standardize roughness;l_(m)=the traverse (scan) length; and y=the absolute value of thelocation of the profile relative to the mean profile height (x-axis).

In other non-limiting aspects, the efficacy of the compositions of thepresent invention can be evaluated by using a skin analog, such as, forexample, MELANODERM™. Melanocytes, one of the cells in the skin analog,stain positively when exposed to L-dihydroxyphenyl alanine (L-DOPA), aprecursor of melanin. The skin analog, MELANODERM™, can be treated witha variety of bases containing the compositions and whitening agents ofthe present invention or with the base alone as a control.Alternatively, an untreated sample of the skin analog can be used as acontrol.

UV absorption of glyceryl/acid or glycol/acid compounds and compositionscontaining the same can be determined by UV absorption assays that aregenerally known to those of ordinary skill in the art.

All of the compounds, compositions, and/or methods disclosed and claimedcan be made and executed without undue experimentation in light of thepresent disclosure. While the compounds, compositions, and methods ofthis invention have been described in terms of certain embodiments, itwill be apparent to those of skill in the art that variations may beapplied to the compounds, compositions, and/or methods and in the stepsor in the sequence of steps of the method without departing from theconcept, spirit and scope of the invention. More specifically, it willbe apparent that certain agents which are both chemically andphysiologically related may be substituted for the agents describedherein while the same or similar results would be achieved. All suchsimilar substitutes and modifications apparent to those skilled in theart are deemed to be within the spirit, scope and concept of theinvention.

REFERENCES

The following references, to the extent that they provide exemplaryprocedural or other details supplementary to those set forth herein, arespecifically incorporated herein by reference.

-   U.S. Pat. No. 2,798,053-   U.S. Pat. No. 4,509,949-   U.S. Pat. No. 5,087,445-   CTFA International Cosmetic Ingredient Dictionary and Handbook,    10^(th) Ed., (2004).-   Organic Chemistry, 5^(th) Ed.-   Packman and Gams, J. Soc. Cos. Chem., 29:70-90, 1978.-   Remington's Pharmaceutical Sciences, 18th Ed. Mack Printing Company,    1289-1329, 1990.

1. A topical skin care composition comprising a compound having thefollowing structure:


2. The composition of claim 1, wherein the composition is an emulsion, acream, a lotion, or an ointment.
 3. The composition of claim 1, whereinthe composition is an anhydrous composition.
 4. The composition of claim1, wherein the composition comprises from about 0.001% to about 20%, byweight, of the compound.
 5. A composition comprising: 0.001% to 20% byweight of a glyceryl salicylate compound having the following structure:

and at least one of a vitamin, a mineral, and essential fatty acid, anamino acid, a flavinoid, or a protein.
 6. A composition comprising (i) acompound having the following structure:

and (ii) a compound having the following structure:

wherein the composition is formulated as an emulsion, cream, or lotion.